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1
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0002554729
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Academic Press Inc.: New York
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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Nicola, M.2
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Maiocchi, L.4
Micheletti, R.5
Geraldo, E.6
Donetti, A.7
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4
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0026624763
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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Longmei, Z.2
Tangsheng, P.3
Huiyan, Z.4
Yan, L.5
Jingyu, S.6
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5
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0000948339
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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Toteberg-Kaulen, S.2
Rapoport, H.3
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For azabicyclo[3.2.1]octanes, see: (a) Lounasmaa, M. The Alkaloids; Academic Press Inc.: New York, 1988; Vol. 33, pp 1-83. (b) Focor, G.; Dharanipragada, R. Nat. Prod. Rep. 1990, 7, 539. (c) Turconi, M.; Nicola, M.; Quintero, M. G.; Maiocchi, L.; Micheletti, R.; Geraldo, E.; Donetti, A. J. Med. Chem. 1990, 33, 2101. (d) Jung, M. E.; Longmei, Z.; Tangsheng, P.; Huiyan, Z.; Yan, L.; Jingyu, S. J. Org. Chem. 1992, 57, 3528. (e) Petersen, J. S.; Toteberg-Kaulen, S.; Rapoport, H. J. Org. Chem. 1984, 49, 2948. (f) Fevig, J. M.; Marquis, R. W.; Overman, L. E. J. Am. Chem. Soc. 1991, 113, 5085.
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Marquis, R.W.2
Overman, L.E.3
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11
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37049041310
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For a previous synthesis of a 1,5-dicyano-substituted azabicyclo-[3.2.1]octane see: Betts, B. E.; Davey, W. J. Chem. Soc. 1961, 1683.
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Betts, B.E.1
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0028149403
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(a) Blagbrough, I. S.; Coates, P. A.; Hardick, D. J.; Lewis, T.; Rowan, M. G.; Wonnacott, S.; Potter, B. V. L. Tetrahedron Lett. 1994, 35, 8705.
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Blagbrough, I.S.1
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Lewis, T.4
Rowan, M.G.5
Wonnacott, S.6
Potter, B.V.L.7
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15
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0028029877
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(b) Coates, P. A.; Blagbrough, I. S.; Rowan, M. G.; Pearson, D. P. J.; Lewis, T.; Potter, B. V. L. Tetrahedron Lett. 1994, 35, 8709.
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Lewis, T.5
Potter, B.V.L.6
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0025160022
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(a) Knochel, P.; Chou, T.; Jubert, C.; Rajagopal, D. J. Org. Chem. 1993, 58, 588.
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23
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3342955564
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note
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At a concentration of 16 mmol, Birch reduction of pyridine 8 with lithium and water, formed the required trisubstituted cyclohex-2-en-1-one 10 and the unrequired tetrasubstituted cyclohex-2-en-1-one (9) in 27% and 20% yields, respectively. With higher concentrations, diminished yields of 9 and 10 were obtained. (Equation Presented)
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24
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12444252645
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Nagata, W.; Hirai, S.; Itazaki, H.; Takeda, K. J. Org. Chem. 1961, 26, 2413.
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25
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0000953585
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Nagata, W.; Sugusawa, T.; Narisada, M.; Wakabayashi, T.; Hayase, Y. J. Am. Chem. Soc. 1967, 89, 1483.
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Hayase, Y.5
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28
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0001232196
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(a) Utimoto, K.; Wakabayashi, Y.; Horrie, T.; Inoue, M.; Shishiyama, Y.; Obayashi, M.; Norzaki, H. Tetrahedron 1983, 39, 967.
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Obayashi, M.6
Norzaki, H.7
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30
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49649145253
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5-Exo-trigonal ring closure of an amide NH group onto a ketone culminating in the formation of 6-methoxy-7-azabicyclo[4.2.1]nona-8-one has been reported, see: Newman, H.; Fields, T. L. Tetrahedron 1972, 28, 4051.
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Fields, T.L.2
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3342948578
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For previous syntheses of (6) see: (a) Cohen, T.; Yu, L. C. J. Am. Chem. Soc. 1983, 105, 2811. (b) Luzzio, F. A.; Moore, W. J. J. Org. Chem. 1993, 58, 2966.
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0000667298
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For previous syntheses of (6) see: (a) Cohen, T.; Yu, L. C. J. Am. Chem. Soc. 1983, 105, 2811. (b) Luzzio, F. A.; Moore, W. J. J. Org. Chem. 1993, 58, 2966.
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35
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0002093756
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0000590706
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Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
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Olefination conjugate additions with phosphonate sulfones to optically active tetrahydropyrans have been described: (a) Davidson, A. H.; Hughes, L. R.; Qureshi, S. S.; Wright, B. Tetrahedron, Lett. 1988, 29, 693. (b) Keck, G. E.; Kachensky, D. F.; Enholm, E. J, J. Org. Chem. 1985, 50, 4317. (c) Bloch, R.; Seck, M. Tetrahedron 1989, 45, 3731. (d) Ali, M. H.; Hough, L.; Richardson, A. C. J. Chem. Soc., Chem. Commun. 1984, 447. (e) Georges, M.; Fraser-Reid, B. J. Org. Chem. 1985, 50, 5754.
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